$149 Cheap Flights from Manchester (MHT) to Chicago (MDW)

View $149 flight on Sat, May 17, 2025Opens in a new window

Popular airlines from Manchester-Boston Regional Airport (MHT) to Chicago Midway Airport (MDW)

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Find available prices by choosing your travel dates.

Cheap Flights from Manchester to Chicago (MHT-MDW)

Prices were available within the past 7 days and start at $149 for one-way flights and $297 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
MHT
Manchester
MDW
Chicago
$297 Roundtrip, found 4 hours ago
$297
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Manchester to Chicago, returning Tue, Jun 10, priced at $297 found 4 hours ago
Southwest Airlines
Sat, May 24 - Tue, May 27
MHT
Manchester
MDW
Chicago
$299 Roundtrip, found 5 days ago
$299
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, May 24 from Manchester to Chicago, returning Tue, May 27, priced at $299 found 5 days ago
Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
MHT
Manchester
MDW
Chicago
$307 Roundtrip, found 4 hours ago
$307
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Manchester to Chicago, returning Tue, Jun 10, priced at $307 found 4 hours ago
Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
MHT
Manchester
MDW
Chicago
$312 Roundtrip, found 4 hours ago
$312
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Manchester to Chicago, returning Tue, Jun 10, priced at $312 found 4 hours ago
Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
MHT
Manchester
MDW
Chicago
$314 Roundtrip, found 4 hours ago
$314
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Manchester to Chicago, returning Tue, Jun 10, priced at $314 found 4 hours ago
Southwest Airlines
Sun, May 25 - Mon, Jun 2
MHT
Manchester
MDW
Chicago
$318 Roundtrip, found 3 days ago
$318
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, May 25 from Manchester to Chicago, returning Mon, Jun 2, priced at $318 found 3 days ago
Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
MHT
Manchester
MDW
Chicago
$324 Roundtrip, found 4 hours ago
$324
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Manchester to Chicago, returning Tue, Jun 10, priced at $324 found 4 hours ago
Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
MHT
Manchester
MDW
Chicago
$327 Roundtrip, found 4 hours ago
$327
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Manchester to Chicago, returning Tue, Jun 10, priced at $327 found 4 hours ago
Southwest Airlines
Sun, May 25 - Mon, Jun 2
MHT
Manchester
MDW
Chicago
$328 Roundtrip, found 3 days ago
$328
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, May 25 from Manchester to Chicago, returning Mon, Jun 2, priced at $328 found 3 days ago
Southwest Airlines
Sat, Jun 7 - Tue, Jun 10
MHT
Manchester
MDW
Chicago
$329 Roundtrip, found 4 hours ago
$329
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Jun 7 from Manchester to Chicago, returning Tue, Jun 10, priced at $329 found 4 hours ago

Frequently asked questions

How much does a flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW) cost?
You can pick up cheap return tickets starting from $339 from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MHT on May 11 2025 and touching down at MDW. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from MHT to MDW?
The cheapest flights from MHT to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
When heading out of Manchester-Boston Regional Airport (MHT), you can get on a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from MHT to MDW?
Book a flight from MHT to MDW with Southwest Airlines. This carrier currently has the lowest one-way fare for this route, starting at $149. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MHT on July 5 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
On average, you can pick from 6 direct weekly flights from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW). To expand your choices, consider flights with layovers. Enter your details on Expedia and then filter your search results to show one stop or more.
What are the most popular departure times for flights from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
More people fly between MHT and MDW at 7 AM than at any other time of day. Rather skip the crowds? Pick a flight outside the busiest times and it’s possible you’ll save on your ticket as well.
What day of the week has the most flights from MHT to MDW?
Friday has the most flights from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW). Consider leaving on this day and you’ll have a greater chance of finding a departure that fits your plans.
What is the earliest flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
The first flight of the day leaving from Manchester-Boston Regional Airport (MHT) is at around 7:15AM UTC-5. Catch this flight and you’ll land at Midway Intl. Airport (MDW) at approximately 8:55AM UTC-6. The overall travel time is 2h 40m.
How long does it take to fly from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
It takes about 2 hours and 40 minutes to travel the 840 mi from MHT to MDW.
What is the best time to fly from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
Opt for a flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures later than this have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Manchester-Boston Regional Airport (MHT)?
If you’re traveling on a direct flight from Manchester-Boston Regional Airport (MHT) to Chicago, Midway Intl. Airport (MDW) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from MHT to MDW shortly before your getaway is usually more expensive. But if you’re flexible with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a MHT to MDW flight and hotel package?
You’ll typically save money by securing a MHT to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it’s simple to manage it all in one convenient place. Once you’ve selected your ideal flights and accommodations, you can add extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Manchester-Boston Regional Airport (MHT) to Midway Intl. Airport (MDW)?
Generally, it’s possible to reschedule or cancel your MHT to MDW flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are possible and if any costs are involved. You’ll also find further details on our Customer Service portal.
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